CH3CH2OCH=CH2, ethylvinylether

H5H6
\ |
C3 - H4
/
H11O1 - C2
\ / | \
C10 = C9H8H7
/ \
H12H13
Tell me about the atomic charges, dipole moment, bond lengths, angles, bond orders,
molecular orbital energies, or total energy.
Tell me about the best Lewis structure.

Atomic Charges and Dipole Moment

O1 charge=-0.293
C2 charge= 0.264
C3 charge=-0.451
H4 charge= 0.120
H5 charge= 0.135
H6 charge= 0.134
H7 charge= 0.018
H8 charge= 0.018
C9 charge= 0.184
C10 charge=-0.709
H11 charge= 0.262
H12 charge= 0.238
H13 charge= 0.077
with a dipole moment of 1.93919 Debye

Bond Lengths:

between O1 and C2: distance=1.452 ang___ between O1 and C9: distance=1.374 ang___
between C2 and C3: distance=1.523 ang___ between C2 and H7: distance=1.109 ang___
between C2 and H8: distance=1.110 ang___ between C3 and H4: distance=1.103 ang___
between C3 and H5: distance=1.103 ang___ between C3 and H6: distance=1.103 ang___
between C9 and C10: distance=1.344 ang___ between C9 and H13: distance=1.101 ang___
between C10 and H11: distance=1.094 ang___ between C10 and H12: distance=1.091 ang___

Bond Angles:

for C3-C2-O1: angle=107.5 deg___ for H4-C3-C2: angle=110.1 deg___
for H5-C3-C2: angle=110.5 deg___ for H6-C3-C2: angle=110.4 deg___
for H7-C2-O1: angle=109.2 deg___ for H8-C2-O1: angle=109.3 deg___
for C9-O1-C2: angle=115.2 deg___ for C10-C9-O1: angle=121.9 deg___
for H11-C10-C9: angle=121.1 deg___ for H12-C10-C9: angle=119.9 deg___
for H13-C9-O1: angle=115.4 deg___

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Bond Orders (Mulliken):

between O1 and C2: order=0.785___ between O1 and C9: order=0.706___
between C2 and C3: order=0.835___ between C2 and H7: order=0.989___
between C2 and H8: order=0.988___ between C3 and H4: order=0.981___
between C3 and H5: order=0.985___ between C3 and H6: order=0.985___
between C9 and C10: order=1.949___ between C9 and H13: order=1.016___
between C10 and H11: order=0.941___ between C10 and H12: order=0.994___

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Best Lewis Structure

The Lewis structure that is closest to your structure is determined. The hybridization of the atoms in this idealized Lewis structure is given in the table below. Please note that your structure can't be well described by a single Lewis structure, because of extensive delocalization.

Hybridization in the Best Lewis Structure

1. A bonding orbital for O1-C2 with 1.9903 electrons
__has 68.26% O 1 character in a sp2.60 hybrid
__has 31.74% C 2 character in a s0.80 p3 hybrid

2. A bonding orbital for O1-C9 with 1.9919 electrons
__has 67.57% O 1 character in a sp2.16 hybrid
__has 32.43% C 9 character in a sp2.77 hybrid

3. A bonding orbital for C2-C3 with 1.9937 electrons
__has 50.88% C 2 character in a sp2.28 hybrid
__has 49.12% C 3 character in a sp2.55 hybrid

4. A bonding orbital for C2-H7 with 1.9895 electrons
__has 57.80% C 2 character in a s0.96 p3 hybrid
__has 42.20% H 7 character in a s orbital

5. A bonding orbital for C2-H8 with 1.9895 electrons
__has 57.81% C 2 character in a s0.96 p3 hybrid
__has 42.19% H 8 character in a s orbital

6. A bonding orbital for C3-H4 with 1.9883 electrons
__has 59.11% C 3 character in a s0.92 p3 hybrid
__has 40.89% H 4 character in a s orbital

7. A bonding orbital for C3-H5 with 1.9912 electrons
__has 59.73% C 3 character in a s0.95 p3 hybrid
__has 40.27% H 5 character in a s orbital

8. A bonding orbital for C3-H6 with 1.9912 electrons
__has 59.73% C 3 character in a s0.95 p3 hybrid
__has 40.27% H 6 character in a s orbital

9. A bonding orbital for C9-C10 with 1.9947 electrons
__has 45.44% C 9 character in a p3 hybrid
__has 54.56% C10 character in a p3 hybrid

10. A bonding orbital for C9-C10 with 1.9923 electrons
__has 51.11% C 9 character in a sp1.31 hybrid
__has 48.89% C10 character in a sp1.59 hybrid

11. A bonding orbital for C9-H13 with 1.9845 electrons
__has 58.25% C 9 character in a sp2.26 hybrid
__has 41.75% H13 character in a s orbital

12. A bonding orbital for C10-H11 with 1.9863 electrons
__has 59.90% C10 character in a sp2.22 hybrid
__has 40.10% H11 character in a s orbital

13. A bonding orbital for C10-H12 with 1.9847 electrons
__has 59.49% C10 character in a sp2.27 hybrid
__has 40.51% H12 character in a s orbital

19. A lone pair orbital for O1 with 1.9735 electrons
__made from a sp1.44 hybrid

20. A lone pair orbital for O1 with 1.8981 electrons
__made from a p-pi orbital ( 99.96% p)

-With core pairs on: O 1 C 2 C 3 C 9 C10 -

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Donor Acceptor Interactions in the Best Lewis Structure

The localized orbitals in your best Lewis structure can interact strongly. A filled bonding or lone pair orbital can act as a donor and an empty or filled bonding, antibonding, or lone pair orbital can act as an acceptor. These interactions can strengthen and weaken bonds. For example, a lone pair donor->antibonding acceptor orbital interaction will weaken the bond associated with the antibonding orbital. Conversly, an interaction with a bonding pair as the acceptor will strengthen the bond. Strong electron delocalization in your best Lewis structure will also show up as donor-acceptor interactions.
Interactions greater than 20 kJ/mol for bonding and lone pair orbitals are listed below.

The interaction of bonding donor orbital, 12, for C10-H11 with the antibonding acceptor orbital, 166, for C9-H13 is 26.0 kJ/mol.

The interaction of bonding donor orbital, 13, for C10-H12 with the antibonding acceptor orbital, 157, for O1-C9 is 34.3 kJ/mol.

The interaction of lone pair donor orbital, 19, for O1 with the antibonding acceptor orbital, 166, for C9-H13 is 28.4 kJ/mol.

The interaction of the second lone pair donor orbital, 20, for O1 with the antibonding acceptor orbital, 159, for C2-H7 is 29.7 kJ/mol.

The interaction of the second lone pair donor orbital, 20, for O1 with the antibonding acceptor orbital, 160, for C2-H8 is 29.7 kJ/mol.

The interaction of the second lone pair donor orbital, 20, for O1 with the antibonding acceptor orbital, 164, for C9-C10 is 153. kJ/mol.

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Molecular Orbital Energies

The orbital energies are given in eV, where 1 eV=96.49 kJ/mol. Orbitals with very low energy are core 1s orbitals. More antibonding orbitals than you might expect are sometimes listed, because d orbitals are always included for heavy atoms and p orbitals are included for H atoms. Up spins are shown with a ^ and down spins are shown as v.

24 ----- 1.752

23 ----- 1.447

22 ----- 1.110


21 ----- -0.602


20 -^-v- -5.374


19 -^-v- -7.992
18 -^-v- -8.017


17 -^-v- -9.127

16 -^-v- -9.391
15 -^-v- -9.403

14 -^-v- -9.804


13 -^-v- -11.10

12 -^-v- -11.80

11 -^-v- -12.64


10 -^-v- -14.16


9 -^-v- -15.34


8 -^-v- -17.82


7 -^-v- -19.33


6 -^-v- -26.20


5 -^-v- -265.7

4 -^-v- -266.2


3 -^-v- -267.6

2 -^-v- -267.9


1 -^-v- -507.2

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Total Electronic Energy

The total electronic energy is a very large number, so by convention the units are given in atomic units, that is Hartrees (H). One Hartree is 2625.5 kJ/mol. The energy reference is for totally dissociated atoms. In other words, the reference state is a gas consisting of nuclei and electrons all at infinite distance from each other. The electronic energy includes all electric interactions and the kinetic energy of the electrons. This energy does not include translation, rotation, or vibration of the the molecule.

Total electronic energy = -232.5073488894 Hartrees

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